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WO2002062807A1 - Diamide d'acide phtalique, son procede de fabrication et son utilisation comme pesticide - Google Patents

Diamide d'acide phtalique, son procede de fabrication et son utilisation comme pesticide Download PDF

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Publication number
WO2002062807A1
WO2002062807A1 PCT/EP2002/000809 EP0200809W WO02062807A1 WO 2002062807 A1 WO2002062807 A1 WO 2002062807A1 EP 0200809 W EP0200809 W EP 0200809W WO 02062807 A1 WO02062807 A1 WO 02062807A1
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WO
WIPO (PCT)
Prior art keywords
methyl
formula
alkyl
spp
stands
Prior art date
Application number
PCT/EP2002/000809
Other languages
German (de)
English (en)
Inventor
Thomas Bretschneider
Christoph Erdelen
Original Assignee
Bayer Cropscience Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE10115406A external-priority patent/DE10115406A1/de
Priority to MXPA03006996A priority Critical patent/MXPA03006996A/es
Priority to BR0206964-4A priority patent/BR0206964A/pt
Priority to EP02703581A priority patent/EP1360190B1/fr
Priority to AT02703581T priority patent/ATE304018T1/de
Priority to IL15704602A priority patent/IL157046A0/xx
Application filed by Bayer Cropscience Ag filed Critical Bayer Cropscience Ag
Priority to DE50204181T priority patent/DE50204181D1/de
Priority to CNB028078209A priority patent/CN1310926C/zh
Priority to KR1020037009780A priority patent/KR100838689B1/ko
Priority to US10/467,018 priority patent/US6835847B2/en
Priority to JP2002563159A priority patent/JP4165808B2/ja
Publication of WO2002062807A1 publication Critical patent/WO2002062807A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages

Definitions

  • the present invention relates to new phthalic acid diamides, a process for their preparation and their use as pesticides.
  • X and Y are independently hydrogen, halogen, cyano, ⁇ itro, alkyl, haloalkyl, alkoxy, haloalkoxy, cycloalkyl, halocycloalkyl, cycloalkyloxy, Halogencycloalkyloxy, -S (O) c j-alkyl, -S (O) c j-haloalkyl or each represent optionally substituted phenyl, phenoxy, heteroaryl or heteroaryloxy,
  • n 1, 2, 3 or 4
  • n 1, 2, 3, 4 or 5
  • R 1 , R 2 , R 3 and R 4 independently of one another represent hydrogen, alkyl, haloalkyl or cycloalkyl
  • R 5 , R 6 and R 7 independently of one another represent alkyl or alkoxy
  • A stands for -S (O) ( j- or oxygen
  • -CRJR 2 - can have the same or different meanings if a is 2, 3 or 4,
  • c stands for 0, 1, 2, 3 or 4 with the proviso that the repeating unit -CR 3 R 4 - can have the same or different meanings if c stands for 2, 3 or 4,
  • d 0, 1 or 2.
  • the Neritatien of the formula (I) can optionally be present in different compositions as geometric and / or optical isomers, regioisomers or configuration isomers or their isomer mixtures. Both the pure isomers and the isomer mixtures are claimed according to the invention.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , A, a, b and c have the meanings given above,
  • the compounds of the formula (I) according to the invention have very good insecticidal properties and can be used both in crop protection and in material protection to control unwanted pests, such as insects and acarids.
  • the phthalic acid diamides according to the invention which contain a silicon atom in the side chain, show very good insecticidal and acaricidal effects with good plant tolerance at the same time.
  • X and Y independently of one another preferably represent hydrogen, halogen, cyano, nitro, C 1 -C 6 -alkyl, C r C 6 -haloalkyl, Cj-Cö-alkoxy, C r C 6 -haloalkoxy, C -C 6 -Cycloalkyl, C 3 -C 6 -Halogencycloalkyl, C 3 -C 6 -cycloalkyloxy, C 3 -C 6 -Halogencycloalkyloxy, -S (O) d -C r C 6 -alkyl, -S (O) d -C r C 6 -haloalkyl or phenyl, phenoxy, heteroaryl or heteroaryloxy which are optionally monosubstituted to tetrasubstituted, identically or differently, by halogen, Cj-Cg
  • X and Y also independently of one another preferably each in each case optionally up to four times, identically or differently by C ] -C6-
  • n is preferably 1, 2 or 3.
  • n is preferably 1, 2, 3 or 4.
  • R 1 , R 2 , R 3 and R 4 independently of one another preferably represent hydrogen, C Co
  • R 5 , R 6 and R 7 independently of one another preferably represent C j -Cg-alkyl or C ⁇ -
  • A preferably represents -S (O) d - or oxygen.
  • a preferably represents 1, 2, 3 or 4 with the proviso that the repeating unit -CR * R 2 - can have the same or different meanings if a represents 2, 3 or 4.
  • b is preferably 0 or 1.
  • c preferably represents 0, 1, 2, 3 or 4 with the proviso that the repeating unit -CR 3 R 4 - can have the same or different meanings if c represents 2, 3 or 4.
  • d preferably represents 0, 1 or 2.
  • X and Y independently of one another particularly preferably represent hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, C ] -C - alkyl, -C-C -haloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms, C. j -C.4 alkoxy, C j -C 4 - haloalkoxy with 1 to 9 fluorine, chlorine and / or bromine atoms, C 3 -Cg-
  • Y also particularly preferably represents in each case optionally up to four times, identically or differently by fluorine, chlorine, bromine, iodine, C ] -C 4 -
  • Alkyl C 1 -C 4 -haloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms,
  • Chlorine and / or bromine atoms substituted phenyl, phenoxy, 5- or 6-membered heteroaryl or heteroaryloxy with 1 to 4 heteroatoms which contain 0 to 4 nitrogen atoms, 0 to 2 non-adjacent oxygen atoms and / or 0 to 2 non-adjacent sulfur atoms (in particular furyl,
  • n particularly preferably represents 1 or 2.
  • R 1 , R 2 , R 3 and R 4 independently of one another are particularly preferably hydrogen, C j -C 4 alkyl, C 1 -C 6 -haloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms or C 3 -C 6 cycloalkyl.
  • R 5 , R 6 and R 7 independently of one another are particularly preferably C 1 -C 4 -alkyl or C 1 -C 3 -alkoxy.
  • b particularly preferably represents 0 or 1.
  • c particularly preferably represents 0, 1, 2 or 3 with the proviso that the repeating unit -CR 3 R 4 - can have the same or different meanings if c represents 2 or 3.
  • d particularly preferably represents 0, 1 or 2.
  • X very particularly preferably represents chlorine, bromine, iodine.
  • Y very particularly preferably represents methyl, ethyl, n-propyl, i-propyl, trifluoromethyl, pentafluoroethyl, n-heptafluoropropyl, i-heptafluoropropyl, trifluoromethoxy or -OCF 2 CF 2 H.
  • Y also very particularly preferably represents in each case optionally one to three times, identically or differently by fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t -Butyl, -CF 3 , -CHF 2 ,
  • -CC1F 2 -CF 2 CHFC1, -CF 2 CH 2 F, -CF 2 CC1 3 , -CH 2 CF 3 , -CF 2 CHFCF 3 , -CH 2 CF 2 H, -CH 2 CF 2 CF 3 , - CF 2 CF 2 H, -CF 2 CHFCF 3 , -OCF 3 , -OCHF 2 , -OCF 2 CF 2 H, -SCF 3 , -SCHF 2 substituted phenoxy, pyridinyloxy or tetrazolyl.
  • n very particularly preferably stands for 1.
  • n very particularly preferably stands for 2.
  • R 1 , R 2 , R 3 and R 4 independently of one another very particularly preferably represent hydrogen, methyl or ethyl.
  • R 5 , R 6 and R 7 independently of one another very particularly preferably represent methyl, ethyl, methoxy or ethoxy.
  • a very particularly preferably stands for 1, 2 or 3 with the proviso that the
  • Repeat unit -CR ⁇ R 2 - can have the same or different meanings if a is 2 or 3.
  • b very particularly preferably represents 0 or 1.
  • c very particularly preferably represents 0, 1 or 2 with the proviso that the
  • Repeat unit -CR 3 R 4 - may have the same or different meanings if c is 2.
  • d very particularly preferably represents 0, 1 or 2.
  • A represents sulfur or oxygen
  • b 0 or 1
  • A represents sulfur or oxygen
  • b represents 0 or 1 and X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , a and c have the meanings given above.
  • A stands for SO or SO 2 .
  • Y 1 and Y 2 independently of one another have the preferred, particularly preferred or very particularly preferred meanings of the radical Y given above,
  • A represents S (O) d or oxygen
  • d 0, 1 or 2
  • X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , a and c have the preferred, particularly preferred or very particularly preferred meanings given above.
  • Y 1 is C 1 -C 4 -alkyl, preferably trifluoromethyl, pentafluoroethyl, n-heptafluoropropyl, i-heptafluoropropyl, particularly preferably i-heptafluoropropyl.
  • Y 2 is methyl.
  • Saturated hydrocarbon residues such as alkyl can also be used in connection with heteroatoms, e.g. in alkoxy, where possible, be straight-chain or branched.
  • Formula (II) provides a general definition of the imides required as starting materials when carrying out the process according to the invention.
  • X, Y, n and m are preferably, particularly preferably or very particularly preferably those meanings which have already been mentioned as preferred, particularly preferred, etc. for these radicals in connection with the description of the compounds of the formula (I) according to the invention were.
  • Imides of the formula (II) are known (cf. EP 0 919 542 A and EP 1 006 107 A).
  • Formula (III) provides a general definition of the silylamines required as starting materials when carrying out the process according to the invention.
  • R 1, R 2, R 3, R 4, R 5, R 6, R 7, A, a, b and c are preferred, particularly preferred and very particularly preferably has those meanings which have already in connection with the description of the compounds of the formula (I) according to the invention were mentioned as preferred, particularly preferred, etc. for these radicals.
  • Silylamines of the formula (III) are known in some cases (cf. Tetrahedron Lett. 1999, 40,
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , a and c have the meanings given above,
  • R 1 and R 2 have the meanings given above,
  • R 3 , R 4 , R 5 , R 6 , R 7 and c have the meanings given above,
  • a diluent e.g. methanol
  • a diluent e.g. methanol
  • Suitable diluents for carrying out the process according to the invention are all customary inert, organic solvents.
  • Halogenated aliphatic, alicyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin can preferably be used; Chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether,
  • Carboxylic acids such as formic acid or acetic acid. It is particularly preferred to work in acetic acid or without a diluent.
  • reaction temperatures can be varied over a wide range when carrying out the process according to the invention. In general, temperatures between 20 ° C and 150 ° C, preferably between 50 ° C and 120 ° C.
  • reaction components in different ratios. nits.
  • the processing takes place according to usual methods. In general, the procedure is such that the reaction mixture is concentrated, taken up in a suitable solvent and the product is freed of any impurities which may still be present by chromatography.
  • the procedure is generally carried out under atmospheric pressure. However, it is also possible to work under increased or reduced pressure.
  • the active compounds according to the invention are suitable, with good plant tolerance and favorable warm-blood toxicity, for combating animal pests, in particular insects, arachnids and nematodes which occur in agriculture, in forests, in the protection of stored products and materials, and in the hygiene sector. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the pests mentioned above include:
  • Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber. From the order of the Diplopoda e.g. Blaniulus guttulatus.
  • Thysanura e.g. Lepisma saccharina.
  • Phthiraptera for example Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp ..
  • Thysanoptera for example Hercinothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella accidentalis.
  • Heteroptera e.g. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp. From the order of the Homoptera e.g. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp. From the order of the Homoptera e.g.
  • Spp Heliothis spp., Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Hofeamannodellailaella, Hofeamannellaella, Tinea pellionella Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cnaphalocerus spp., Oulema oryzae.
  • Plant-parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaph.
  • the compounds of the formula (I) according to the invention are distinguished in particular by an excellent action against caterpillars, beetle larvae, spider mites, aphids and leaf miners.
  • the compounds according to the invention can also be used in certain concentrations or application rates as herbicides and microbicides, for example as fungicides, antifungals and bactericides. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active compounds.
  • all plants and parts of plants can be treated. Plants are understood here to mean all plants and plant populations, such as desired and unwanted wild plants or crop plants (including naturally occurring crop plants). Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights. Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves,
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space using the customary treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular in the case of seeds, furthermore by single- or multi-layer coating.
  • the active compounds according to the invention can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances ,
  • formulations are prepared in a known manner, for example by mixing the active compounds according to the invention with extenders, that is to say liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents.
  • extenders that is to say liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.
  • surface-active agents ie emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils
  • Alcohols such as butanol or glycol, and their ethers and esters
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • Possible solid carriers are: e.g. Ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g.
  • nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can be present in commercially available formulations and in the use forms prepared from these formulations in a mixture with other active compounds, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc.
  • Fungicides aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole,
  • Debacarb dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomo h, diniconazole, diniconazol-M, dinocap, diphenylamine, dipyrithipne, ditalimfos, dorphianon, dithianon
  • Imazalil Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan, Iso-valedione, Kasugamycin, Kresoxim-methyl, copper hydroxides, copper-preparations, such as: copper , Copper oxide, oxin copper and Bordeaux mixture,
  • Mancopper Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin,
  • Nickel-dimethyldithiocarbamate Nitrothal-isopropyl, Nuarimol, Ofurace, Oxadixyl, Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin, Paclobutrazol, Pefurazoat, Penconazol, Pencycuron, Phosdiphen, Pimaricinidazonamol, Prozoloxin, Prozoloxin, Prozolamin, Prozolamin, Prozolamin, Prozolamin, Prozolamin, Prozolamin, Prozolin, Chloro nosine sodium, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur, quinconazole, quintozen (PCNB), sulfur and sulfur preparations, tebuconazole, tecloftalara, tecnazen, tetcyclacis, tetraconazolate, tetraconazolate, te
  • Dagger G OK-8705, OK-8801, ⁇ - (1, 1-dimethylethyl) -ß- (2-phenoxyethyl) - 1 H- 1, 2,4-triazole-1-ethanol, ⁇ - (2,4-dichlorophenyl) -ß-fluoro-ß-propyl-lH-l, 2,4-triazole-l-ethanol, ⁇ - (2,4-dichlorophenyl) -ß-methoxy- ⁇ -methyl- lH-l, 2,4-triazole-l-ethanol, ⁇ - (5-methyl-l, 3-dioxan-5-yl) -ß - [[4- (trifluoromethyl) phenyl] methylene] -lH- l, 2,4-tri-azole-1-ethanol, (5RS, 6RS) -6-hydroxy-2,2JJ-tetramethyl-5- (lH-l, 2,4-triazol-l-yl) -3- o
  • N- (2-chloro-4-nitrophenyl) -4-methyl-3-nitro-benzenesulfonamide N- (4-cyclohexylphenyl) -1, 4,5,6-tetrahydro-2-pyrimidinamine, N- (4-hexylphenyl ) - 1, 4,5,6-tetrahydro-2-pyrimidinamine, N- (5-chloro-2-methylphenyl) -2-methoxy-N- (2-oxo-3-oxazolidinyl) acetamide, N- (6 Methoxy) -3-pyridinyl) -cyclopropanecarboxamide,
  • Fenamiphos Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate, Fipronil, Fluazuron, Flubrocythrinate, Flucycloxuron, Floxthrinate, Foncyoxhrhronate, Fufenoxthhronate, Fufenoxin, Fufone - thiocarb,
  • Halofenozide HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene, Imidacloprid, isazofos, isofenphos, isoxathion, ivermectin,
  • Metolcarb Metoxadiazone, Mevinphos, Milbemectin, Monocrotophos,
  • Paecilomyces fumosoroseus Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A,
  • Pirimiphos M Profenofos, Promecarb, Propoxur, Prothiofos, Prothoat, Pymetrozine,
  • Tefluthrin Temephos, Temivinphos, Terbufos, Tetrachlorvinphos, Theta-cyper-methrin, Thiamethoxam, Thiapronil, Thiatriphos, Thiocyclam hydrogen oxalate, Thiodicarb, Thiofanox, Thuringiensin, Tralocythrin, Tralometene
  • Triazamates triazophos, triazuron, trichlophenidines, trichlorfon, triflumuron,
  • the active compounds according to the invention can furthermore be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists.
  • Synergists are compounds through which the action of the active compounds according to the invention is increased without the added synergist itself having to be active.
  • the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight.
  • the application takes place in a customary manner adapted to the application forms.
  • the active ingredient When used against hygiene pests and pests of stored products, the active ingredient is distinguished by an excellent residual action on wood and clay and by a good stability to alkali on limed substrates.
  • Protoplast fusion obtained plant species and plant varieties and their parts treated.
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetic modified organisms) and their parts are treated.
  • Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.
  • Plant cultivars are understood to mean plants with certain properties (“traits”) which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be cultivars, bio- and genotypes.
  • the treatment according to the invention can also have additive (“synergistic”) effects. For example, reduced application rates and / or extensions of the i
  • the preferred transgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which, through the genetic engineering modification, have received genetic material which contains them
  • traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of Ripe, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products.
  • Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses and an increased tolerance of the plants to certain herbicides
  • transgenic plants are the important cultivated plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed and fruit plants (with the fruits of apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes and cotton and rapeseed are highlighted.
  • insects which are particularly emphasized are the plants' increased defense against insects by toxins arising in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes Cry ⁇ A (a), Cry ⁇ A (b), Cry ⁇ A (c), CryllA, CrylllA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants”).
  • the increased resistance of plants against fungi, bacteria and viruses through systemic acquired resistance (SAR), systemin, phytoalexins, and elicitors are also particularly emphasized as properties (“traits”) as well as resistance genes and correspondingly expressed proteins and toxins.
  • the properties (“traits”) which are particularly emphasized are the increased tolerance of the plants to certain herbicidal active compounds, for example imidazoline, sulfonylureas, glyphosate or phosphinotricin (for example “PAT” gene).
  • the genes conferring the desired properties (“traits”) can also be found in combinations with one another in the transgenic plants.
  • Bt plants are maize varieties, cotton varieties, soy varieties and potato varieties that are marketed under the trade names YIELD GARD® (eg maize , Cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato).
  • YIELD GARD® eg maize , Cotton, soy
  • KnockOut® e.g. corn
  • StarLink® e.g. corn
  • Bollgard® cotton
  • Nucotn® cotton
  • NewLeaf® potato
  • herbicide-tolerant plants are corn varieties, cotton varieties and soy varieties which are marketed under the trade names Roundup Ready® (tolerance against glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance against phosphinotricin, e.g. rapeseed), IMI® (tolerance against Imidazolinone) and STS® (tolerance to sulfonylureas such as maize).
  • the herbicide-resistant plants (conventionally bred to herbicide tolerance) include the varieties sold under the name Clearfield® (e.g. maize). Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties (“traits”).
  • plants listed can be treated particularly advantageously according to the invention with the compounds of the general formula (I) or the active compound mixtures according to the invention.
  • the preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.
  • the active compounds according to the invention act not only against plant, hygiene and stored-product pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, Hairlooms, featherlings and fleas.
  • animal parasites ectoparasites
  • ectoparasites such as tick ticks, leather ticks, mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, Hairlooms, featherlings and fleas.
  • parasites include: From the order of the Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp ..
  • Nematocerina and Brachycerina e.g. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp.,
  • Hybomitra spp. Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp ., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp ..
  • Siphonaptrida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp ..
  • Amblyomma spp. Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumoniassus spp., Stemostoma spp., Varroa spp ..
  • ticks such as Amblyomma hebraeum
  • parasitic flies such as against Lucilia cuprina
  • fleas such as Ctenocephalides felis.
  • the active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are used in agricultural animals, e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, house birds, aquarium fish and so-called experimental animals, such as Infest hamsters, guinea pigs, rats and mice. By fighting these arthropods, deaths and
  • the active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, for example by Injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or
  • Bathing dipping
  • spraying spray
  • pouring on pour-on and spot-on
  • washing pumping in and with the help of shaped articles containing active ingredients, such as necklaces, ear tags, tail tags, limb tapes, holders, marking devices, etc.
  • the active compounds of the formula (I) according to the invention can be used as formulations (for example powder, emulsions ions, flowable agents), which contain the active compounds according to the invention in an amount of 1 to 80% by weight, directly or after 100 to 10,000-fold dilution or use them as a chemical bath.
  • formulations for example powder, emulsions ions, flowable agents
  • Lyctus brunneus Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus.
  • Hymenoptera such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur.
  • Kalotermes flavicollis Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.
  • Bristle tails such as Lepisma saccharina.
  • non-living materials such as preferably plastics, adhesives, glues, papers and cartons, leather, wood, wood processing products and paints.
  • the material to be protected against insect infestation is very particularly preferably wood and wood processing products.
  • Wood and wood processing products which can be protected by the agent according to the invention or mixtures containing it are to be understood as examples:
  • the active compounds according to the invention can be used as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or pastes.
  • the formulations mentioned can be prepared in a manner known per se, e.g. by mixing the active ingredients according to the invention with at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, water repellant, optionally siccatives and UV stabilizers and optionally dyes and pigments and further processing aids.
  • the insecticidal compositions or concentrates used to protect wood and wood-based materials contain the active compound according to the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.
  • the amount of the agents or concentrates used depends on the type and occurrence of the insects and on the medium. The optimal amount can be determined in each case by test series. In general, however, it is sufficient to use 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active compound, based on the material to be protected.
  • the organic chemical solvents used are preferably oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C.
  • Corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene, are used as such poorly volatile, water-insoluble, oily and oily solvents.
  • Mineral oils with a boiling range of 170 to 220 ° C, test gasoline with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° C are advantageous. Te ⁇ entinöl and the like. For use.
  • the organic non-volatile oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C can be partially replaced by slightly or medium-volatile organic chemical solvents, with the proviso that the solvent mixture also has an evaporation number 35 and a flash point above 30 ° C, preferably above 45 ° C, and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture.
  • part of the organic chemical solvent or solvent mixture or an aliphatic polar organic chemical solvent or solvent mixture is replaced.
  • Aliphatic organic chemical solvents containing hydroxyl and / or ester and / or ether groups such as, for example, glycol ethers, esters or the like, are preferably used.
  • the known organic-chemical binders are water-thinnable and / or soluble or dispersible or emulsifiable in the organic-chemical solvents used
  • Synthetic resins and / or binding drying oils in particular binders consisting of or containing an acrylate resin, a vinyl resin, e.g. Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene-coumarone resin, silicone resin, drying vegetable and / or drying oils and or physically drying binders based on a natural and / or Resin used.
  • binders consisting of or containing an acrylate resin, a vinyl resin, e.g. Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene-coumarone resin, silicone resin, drying vegetable and / or drying oils and or physically drying binders based on a natural and / or Resin used.
  • the synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellants, odor correctors and inhibitors or anticorrosive agents and the like can be used.
  • At least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably contained in the agent or in the concentrate as the organic chemical binder.
  • Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention.
  • binder mentioned can be replaced by a fixing agent (mixture) or a plasticizer (mixture). These additions are said to be one Prevent volatilization of the active ingredients as well as crystallization or precipitation. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).
  • the plasticizers come from the chemical classes of phthalic acid esters such as
  • phosphoric acid esters such as tributyl phosphate
  • adipic acid esters such as di (2-ethylhexyl) adipate
  • stearates such as butyl stearate or amyl stearate
  • oleates such as butyl oleate, glycerol ether or higher molecular weight glycol ether, tolcerol sulfate and
  • Fixing agents are chemically based on polyvinyl alkyl ethers such as e.g. Polyvinyl methyl ether or ketones such as benzophenone, ethylene benzophenone.
  • Water is also particularly suitable as a solvent or diluent, if appropriate in a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants.
  • a particularly effective wood protection is achieved through industrial impregnation processes, e.g. Vacuum, double vacuum or pressure process.
  • the ready-to-use compositions can optionally contain further insecticides and, if appropriate, one or more fungicides.
  • insecticides and fungicides mentioned in WO 94/29 268 are preferably suitable as additional mixing partners.
  • the compounds mentioned in this document are an integral part of the present application.
  • Insecticides such as Chlo ⁇ yriphos, Phoxim, Silafluofin, Alphamethrin, Cyfluthrin, Cypermethrin, Deltamethrm, Permethrin, Imidacloprid, NI-25, Flufenoxuron, Hexaflumuron, Transfluthridon, as well as Thiffenciduron, as well as Funglumiduron, as well as Funglumiduron, as well as Funglumiduron, as well as Funglizidopuron, as well as Funglizidopuron, as well as Funglizidopuron, as well as Funglizidopuron, as well as Funglizidopuron, as well as Funglizidophronid, as well as Funglizidopuron, as well as Funglizido
  • the compounds according to the invention can be used to protect objects, in particular hulls, sieves, nets, structures,
  • Scalpellum species or by species from the group Balanomo ⁇ ha (barnacles), such as Baianus or pollicipes species, increases the frictional resistance of ships and consequently leads to a significant increase in operating costs due to increased energy consumption and, moreover, frequent dry dock stays.
  • heavy metals such as, for example, in bis (tri-alkyltin) sulfides, tri-rc-butyltin laurate, tri- / ⁇ -butyltin chloride, copper (I) oxide , Triethyltin chloride, tri - «- butyl (2-phenyl-4-chl ⁇ henoxy) tin, tributyltin oxide, molybdenum disulfide, antimony oxide, polymeric butyl titanate, phenyl- (bispyridine) - bismuth chloride, tri-n-butyltin fluoride, manganese ethylene, zinc thiocarbamate carbamate, zinc thiocarbamate carbamate , Zinc and copper salts of 2-pyridinthiol-1-oxide, bisdimethyldithiocarbamoylzinkethylenbisthiocarbamat, zinc
  • the ready-to-use antifouling paints can also be used if necessary
  • Contain active ingredients preferably algicides, fungicides, herbicides, molluscicides or other antifouling agents.
  • Suitable combination partners for the antifouling agents according to the invention are preferably:
  • Fentin acetate, metaldehyde, methiocarb, niclosamide, thiodicarb and trimethacarb; or conventional antifouling agents such as
  • the antifouling agents used contain the active ingredient according to the invention of the compounds according to the invention in a concentration of 0.001 to 50% by weight, in particular 0.01 to 20% by weight.
  • the antifouling agents according to the invention further contain the usual ingredients such as e.g. in Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, Park Ridge, 1973.
  • antifouling paints contain in particular binders.
  • Examples of recognized binders are polyvinyl chloride in a solvent system, chlorinated rubber in a solvent system, acrylic resins in a solvent system, in particular in an aqueous system, vinyl chloride / vinyl acetate copolymer systems in the form of aqueous dispersions or in the form of organic solvent systems, butadiene / styrene / acrylonitrile Rubbers, drying oils, such as linseed oil, resin esters or modified hard resins in combination with tar or bitumen, asphalt and epoxy compounds, small amounts of chlorinated rubber, chlorinated polypropylene and vinyl resins.
  • Paints may also contain inorganic pigments, organic pigments or dyes, which are preferably insoluble in sea water. Paints may also contain materials such as rosin to enable controlled release of the active ingredients.
  • the paints can also contain plasticizers, modifiers that influence the theological properties, and other conventional components.
  • the compounds according to the invention or the abovementioned mixtures can also be incorporated into self-polishing antifouling systems.
  • the active compounds according to the invention are also suitable for controlling animal
  • Pests especially insects, arachnids and mites, which live in closed spaces such as apartments, factories, offices, vehicle Cabins occur among other things.
  • they can be used alone or in combination with other active ingredients and auxiliaries in household insecticide products. They are effective against sensitive and resistant species and against all stages of development.
  • These pests include:
  • Sco ⁇ ionidea e.g. Buthus occitanus.
  • Acarina e.g. Argas persicus, Argas reflexus, Bryobia spp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipi- cephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophageides pteronissimus, Dermatophagoides forinae.
  • Opiliones e.g. Pseudosco ⁇ iones chelifer, Pseudosco ⁇ iones cheiridium, Opiliones phalangium.
  • Isopoda e.g. Oniscus asellus, Porcellio scaber.
  • Diplopoda e.g. Blaniulus guttulatus, Polydesmus spp ..
  • Psocoptera for example Lepinatus spp., Liposcelis spp.
  • Coleptera for example Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum.
  • Aedes aegypti Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fann Musca domestica, Phlebotomus spp., Sarcophaga camaria, Simulium spp., Stomoxys calcitrans, Tipula paludosa.
  • Lepidoptera e.g. Achroia grisella, Galleria mellonella, Plodia inte ⁇ unctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
  • Siphonaptera e.g. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
  • Hymenoptera e.g. Camponotus herculeanus, Lasius fiuginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
  • anoplura e.g. Pediculus humanus capitis, Pediculus humanus co ⁇ oris, Phthirus pubis.
  • the specified logP values were determined in accordance with EEC Directive 79/831 Annex N.A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal column (C 18). Temperature: 43 ° C.
  • the determination is carried out in the acidic range at pH 2.3 with 0.1% aqueous phosphoric acid and acetonitrile as eluents; linear gradient from 10% acetonitrile to 90% acetonitrile.
  • the calibration was carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values on the basis of the retention times by linear interpolation between two successive alkanones).
  • the lambda max values were determined using the UN spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • Soybean shoots (Glycine max) are treated by immersing them in the active ingredient preparation of the desired concentration and populating them with Heliothis virescens caterpillars while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with larvae of the horseradish leaf beetle (Phaedon cochleariae) while the leaves are still moist.
  • the kill is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • Cabbage leaves (Brassica oleracea) are treated by dipping into the preparation of active ingredient of the desired concentration and populated with caterpillars of the cabbage cockroach (Plutella xylostella, sensitive stem) while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the cabbage cockroach (Plutella xylostella, resistant stem) while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the army worm (Spodoptera exigua) while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the army worm (Spodoptera frugiperda) while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Emulsifier 1 part by weight of alkylaryl polyglycols
  • Amount of emulsifier and dilute the concentrate with water to the desired concentration is required.
  • the active ingredient preparation is poured onto the floor.
  • the concentration of the active ingredient in the preparation is practically irrelevant, the only decisive factor is the amount of active ingredient per unit volume of soil, which is given in ppm (mg / 1). You fill the bottom in 0.25 1 pots and let them stand at 20 ° C.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Soybean shoots (Glycine max) of the Roundup Ready variety (trademark of Monsanto Comp. USA) are treated by dipping into the preparation of active compound of the desired concentration and populated with the tobacco bud caterpillar Heliothis virescens while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un nouveau diamide d'acide phtalique de formule (I), dans laquelle X, Y, n, m, R<1>, R<2>, R<3>, R<4>, R<5>, R<6>, R<7>, A, a, b et c ont les significations données dans la description, ainsi qu'un procédé de fabrication de ces produits et leur utilisation dans la lutte contre les animaux nuisibles.
PCT/EP2002/000809 2001-02-06 2002-01-25 Diamide d'acide phtalique, son procede de fabrication et son utilisation comme pesticide WO2002062807A1 (fr)

Priority Applications (10)

Application Number Priority Date Filing Date Title
JP2002563159A JP4165808B2 (ja) 2001-02-06 2002-01-25 フタル酸ジアミド、該生成物の製造方法及び害虫を駆除するためのその使用
BR0206964-4A BR0206964A (pt) 2001-02-06 2002-01-25 Diamidas de ácido ftálico, um processo para a sua preparação e sua aplicação como composições praguicidas
EP02703581A EP1360190B1 (fr) 2001-02-06 2002-01-25 Diamide d'acide phtalique, son procede de fabrication et son utilisation comme pesticide
AT02703581T ATE304018T1 (de) 2001-02-06 2002-01-25 Phthalsäurediamide, ein verfahren zu ihrer herstellung und ihre verwendung als schädlingsbekämpfungsmittel
IL15704602A IL157046A0 (en) 2001-02-06 2002-01-25 Phthalic acid diamide, method for the production thereof and the use of the same as a pesticide
MXPA03006996A MXPA03006996A (es) 2001-02-06 2002-01-25 Diamidas del acido ftalico, procedimiento para su obtencion y su uso como agentes pesticidas.
DE50204181T DE50204181D1 (de) 2001-02-06 2002-01-25 Phthalsäurediamide, ein verfahren zu ihrer herstellung und ihre verwendung als schädlingsbekämpfungsmittel
CNB028078209A CN1310926C (zh) 2001-02-06 2002-01-25 邻苯二甲酰胺类化合物、它们的制备方法和它们作为杀虫剂的应用
KR1020037009780A KR100838689B1 (ko) 2001-02-06 2002-01-25 프탈산디아미드, 그의 제조방법 및 살충제로서의 그의 용도
US10/467,018 US6835847B2 (en) 2001-02-06 2002-01-25 Phthalic acid diamide, method for the production thereof and the use of the same as a pesticide

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE10105169 2001-02-06
DE10105169.7 2001-02-06
DE10115406A DE10115406A1 (de) 2001-02-06 2001-03-29 Phthalsäurediamide
DE10115406.2 2001-03-29

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US (1) US6835847B2 (fr)
EP (1) EP1360190B1 (fr)
JP (1) JP4165808B2 (fr)
CN (1) CN1310926C (fr)
AT (1) ATE304018T1 (fr)
BR (1) BR0206964A (fr)
DE (1) DE50204181D1 (fr)
ES (1) ES2245398T3 (fr)
IL (1) IL157046A0 (fr)
MX (1) MXPA03006996A (fr)
WO (1) WO2002062807A1 (fr)

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WO2004033468A1 (fr) * 2002-10-04 2004-04-22 E.I. Du Pont De Nemours And Company Insecticides anthranilamide
EP1974606A2 (fr) 2004-07-20 2008-10-01 Bayer CropScience AG Insecticides sélectifs à base de phtalamides et de phytoprotecteurs
US8143193B2 (en) 2003-07-08 2012-03-27 Bayer Cropscience Ag Active agents combination exhibiting insecticidal and acaricide properties

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BR0313943A (pt) * 2002-08-26 2005-08-02 Nissan Chemical Ind Ltd Composto benzanilida substituìdo e agente de controle de organismo nocivo
DE10330723A1 (de) * 2003-07-08 2005-02-03 Bayer Cropscience Ag Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften
JP2005114718A (ja) * 2003-10-10 2005-04-28 Bayer Cropscience Ag 殺虫剤活性化合物を特定するための方法
DE102005059466A1 (de) * 2005-12-13 2007-06-14 Bayer Cropscience Ag Insektizide Zusammensetzungen mit verbesserter Wirkung
MX2009003071A (es) * 2006-09-30 2009-04-02 Bayer Cropscience Ag Mejora del efecto biologico de composiciones agroquimicas en la aplicacion al sustrato de cultivo, formulaciones adecuadas y su uso.
KR101538811B1 (ko) * 2007-04-03 2015-07-22 이 아이 듀폰 디 네모아 앤드 캄파니 치환된 벤젠 살진균제
US7652116B2 (en) * 2007-06-20 2010-01-26 3M Innovative Properties Company Fluorochemical urethane-silane compounds and aqueous compositions thereof
JP6269875B2 (ja) * 2017-03-09 2018-01-31 信越化学工業株式会社 有機ケイ素化合物およびその製造方法

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WO2004033468A1 (fr) * 2002-10-04 2004-04-22 E.I. Du Pont De Nemours And Company Insecticides anthranilamide
US7211270B2 (en) 2002-10-04 2007-05-01 E. I. Du Pont De Nemours And Company Anthranilamide insecticides
CN100349901C (zh) * 2002-10-04 2007-11-21 纳幕尔杜邦公司 邻氨基苯甲酰胺杀虫剂
US8143193B2 (en) 2003-07-08 2012-03-27 Bayer Cropscience Ag Active agents combination exhibiting insecticidal and acaricide properties
EP1974606A2 (fr) 2004-07-20 2008-10-01 Bayer CropScience AG Insecticides sélectifs à base de phtalamides et de phytoprotecteurs

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ATE304018T1 (de) 2005-09-15
MXPA03006996A (es) 2003-11-18
EP1360190A1 (fr) 2003-11-12
ES2245398T3 (es) 2006-01-01
JP4165808B2 (ja) 2008-10-15
US6835847B2 (en) 2004-12-28
DE50204181D1 (de) 2005-10-13
EP1360190B1 (fr) 2005-09-07
CN1500092A (zh) 2004-05-26
BR0206964A (pt) 2004-03-09
IL157046A0 (en) 2004-02-08
US20040077597A1 (en) 2004-04-22
JP2004526703A (ja) 2004-09-02

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